


Clockwork

by Sterekaddict



Category: Teen Wolf (TV)
Genre: Correctional officer Derek Hale, Derek Hale/ Stiles Stilinski - Freeform, Drug Dealing, Drug Lord Stiles Stilinski, Injured Stiles, M/M, Murder, Prison, Sexual Harassment, Shanks made from weird things, drug lord, prison riots, sharing memories, shitty prison guards
Language: English
Status: Completed
Published: 2015-06-23
Updated: 2015-08-11
Packaged: 2018-04-05 18:34:50
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 10
Words: 14,797
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4190583
Author URL: https://archiveofourown.org/users/Sterekaddict/pseuds/Sterekaddict
Summary: <blockquote class="userstuff">
              <p>Stiles never intended to be the biggest, best known drug lord across the state of California, it just kind of happened.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> The idea for this fic was given to me by a friend but I'm having a hard time starting it out but I hope you enjoy what I have and what will come later on! 
> 
> EDIT: 6-24-15  
> I have/am in the process of rewriting a lot of things so you might wanna go ahead and re read the whole thing, someone told me they felt like a lot of things were missing and I admit I haven't put a lot of effort into this story as I have for my other ones so please be patient with me until I get it sorted out for you guys! I love hearing all your comments so I promise I'll try harder to make this story lovely for all of you. As far as I know chapters 1 & 2 will stay the same for the most part but I will be rewriting chapters 3 & 4\. I'm not sure when they will be finished but I will try and get it done for you guys. Thank you.

Stiles never intended to be the biggest and best known drug lord in the state of California, it just kind of happened.

*

He was in the wrong place at the wrong time. Stiles had just turned 19 when he walked in on a drug deal going on in the alley near his work. There 2 men with guns, and one man on the ground who had been knocked unconscious. Stiles’ eyes widened as the men turned towards him. He tripped backing away as the bigger, burly man had walked towards him, grabbing under his chin with one gigantic hand.

The man shoves Stiles up against the wall, knocking the air from his lungs. Stiles coughs violently, struggling to get out of the mans grip. 

“O-okay man listen I didn’t m-mean to walk in on this.” Stiles stutters from lack of air in his lungs. 

The bigger man smirks before looking Stiles right in the eye. “It's him.” He says, directed towards his partner. 

*

Stiles was put in a large van, but he wasn’t tied up or gagged or anything to keep from speaking or to see where they were taking him. 

“Hey uh so are you guys taking me back to your base or something? I don’t know what you’re gonna do with me, I’m nothing special. I mean c’mon.” Stiles presses his lips into a line and crosses his arms over his chest. 

“Shut up.” The smaller man says before looking back at the window. 

The van pulls to a stop about half an hour later, the back door opening, flooding the van with sunlight. Stiles covers his eyes slightly with his hand, as he’s led out of the van and into a fancy looking building. There are people on all sides of him, each of them with guns somewhere on their bodies. They don’t touch Stiles as he moves, they just lead him to an elevator and then press the button for the highest floor. 

The men lead him to what seems to be the biggest room in the building. Stiles looks around the room, its very nicely furbished with suede couches and expensive looking paintings and vases placed around. Stiles looks directly ahead of him to see a very old man, in a nice suit. He doesn’t look too good. He gestures for Stiles to come forward. Stiles glances around nervously, before walking to the old man and sitting in a small chair next to him. 

“Mr. Stilinski I presume?” 

“Yeah that’s me, how’d you know my name?” Stiles asks, having no recollection of meeting this man before in his life. He swallows nervously as the man continues to speak, his voice low and weak, like he’s on the verge of dying. 

“I’ve been watching you, you’re very smart and I want you to carry on for me.” The man smiles weakly showing perfectly white teeth. Totally dentures, for a guy this old? There’s no way his teeth are that great. 

“Carry on this business? Like be the new drug lord guy? Cause that sounds dangerous but hey the money cant be too bad I mean look at this place, and that suit, and all your guns and stuff. Must have cost a fortune.” 

The man nods and chuckles a bit before speaking again. 

“Yes all that is very true, but the thing is, you’re special and I know you can make my business thrive again after I die! I presume you at least know something about the drug cartel huh boy? I know you can do this for me.” The man covers his mouth and coughs hard, before pulling his hand away covered with blood.

Stiles nods fervently, before standing and walking around the room the look at the papers sprawled on the tables, red lines drawn on them for what seems to be delivery trails. 

“Man do you guys not know California at all?” Stiles points to a spot on the map. “The deputies in this area patrol here quite often so that’s a bad spot, you’d want to move it and take it through here where its deserted, but you’d still be able to reach the delivery destination.” Stiles says, dragging his finger in a more logical route. Stiles turns around to see everyone looking at him. 

“So yeah when do I start? Right now? Tomorrow? Sometime soon? Cause if you wanna get this shit booming you guys really need to re-evaluate almost all of your routes and tactics for delivery.” Stiles shrugs and smiles a little at the old man. “You haven’t done a bad job so far but you can totally improve everything.” 

“You can start anytime you want.” The old man says before being taken from the room. 

Stiles turns to the people left in the room. “Great so I’ll be back tomorrow, you guys should know where I’ll be” Stiles walks out leaving the men and women behind. 

*

Stiles is laying in his dorm bedroom later that night, looking up things on the old mans business. Or what’s left of it. He used to be really huge back in the day, but most of his people had been caught or murdered, and apparently he’s on the FBI most wanted list. 

Stiles smiles a little thinking of all the power he could have at his disposal. But what if its hard? Stiles doesn’t even do drugs okay but navigating all the people who work for him now shouldn’t be too hard. Stiles pulls out his phone and decides to shoot a group text to Scott, Allison, Lydia, and Isaac, telling them everything that’s happened and that if they decided to help him out with it, he would give them (insert obscene amount of money here) once he’s earned it. 

He knows Scott and Isaac would agree, both of them sick of interning for this narcissistic douche who’s ego is probably bigger than his dick. He gets texts back from every one later saying they agree and they would love to help out. 

*

Stiles returns the next day with the gang, introducing them to everyone and then getting right down to work, rerouting the delivery system, directing people to get right to work on delivering. 

“Okay so make sure whoever gives you shit about the way I run this shit or anyone who doesn’t pay up the way they’re suppose to, you deal with them.” Stiles smirks as he takes his seat at the front of the biggest room, looking down on his people.


	2. Chapter 2

**Notes for the Chapter:**

> There are murder scenes in this chapter, details of them as well so be cautious if that's something that bothers you!
> 
> Also please remember my previous note from Chapter 1, I am having a hard time starting this out but once I get to the point I want I feel it will be better written so please bear with me until then and enjoy!

Stiles turns on his tv to see that he's on the news again. He had just taken out someone who was causing a huge threat to his business and the country, see Stiles does goodsometimes. His face breaks out into a smile, as he gets dressed pulling a fancy suit , along with some beat up converse. They're much more comfortable than dress shoes and easier to get away in if he needs to. Today Stiles just knows he's gonna get to finally do some dirty work.   
*  
He's on his way to associate with a new client, one he knows has been trying to tear him down since he started getting more popular, essentially stealing his customers (of course not meaning to). The drive is painfully slow, he’s anxious but he knows he’ll be able to do some good for his business. Its not like Stiles hadn’t killed anyone before so this guy shouldn’t be that hard to take out.

He arrives at the scene, and looks around to see its very secluded and there aren’t any security cameras anywhere on the building. Before stepping off the van he slides a pistol into the back of his dress pants, pulling his blazer over the back to conceal it.

“Whish me good luck Scotty” Stiles makes a small salute before walking inside. 

He straightens the blazer as he walks into the building the meeting is being held at. He nods a greeting at some people working there before making his way to a room on the 10th floor, that's made from glass. He steps into the room and takes a seat across from his client who goes by Howell.

"Lets get down to business shall we?" Stiles says with a deadly smirk on his face. 

He takes a seat across from Howell who supposedly wants to join up with him, to take their product across the country for more business. Stiles listens, nodding at propositions Howell suggests to make their business expand with the help of him and the others he is working with. 

"Here's what's gonna happen. By expanding the amount of people we work with across the country we will be able to distribute and produce twice the amount of product you are making now.” Howell says, reaching under the desk to grab something taped to the bottom. Before he can reach it Stiles has already pulled out his gun and taken the safety off before pointing it at the mans head. 

"Do you really think I am that stupid to believe you want to join with me to expand the business? I know all your dirty little secrets Howell, and I am not an easy man to fool," Stiles whips the man across the face with the butt of his pistol before grabbing the gun from under the desk and unloading it before tossing it to the side.

"Don't you know who I am? What I really do?" Stiles points the gun back at Howells face. "I must say the way you approached me wasn’t as stupid as it could’ve been," Stiles steps on Howells chest to hold him down and keep him from moving. "But I knew who you were before you even got into this scene." Stiles laughs loudly, wiping a fake tear from his eye. 

"F-fuck you!" Howell tries to spit back at Stiles only succeeding to get a mouth full of his own blood on his face  
.   
"You're really gonna wish you hadn't crossed me, bitch." Stiles pulls the trigger, blood and brains splattering on his light gray suit and the glass walls next to him. Stiles wipes a splatter of blood from his cheek before stashing his pistol away and leaving the room. 

The employees who are in the building give Stiles horrified looks as he walks by, but he's just smirking at them, pulling out his gun as he sees a woman reaching in the drawer of her desk. Stiles clicks his tongue and shakes his head at her before pulling the trigger of his gun, making the woman fall against the wall, leaving a trail of blood as she slides down to the floor. Stiles puts on his best smile as he walks out of the building and back to his van where Scott is waiting for him. 

“Dude gross is that brain?” Scott asks, driving the van back to their HQ. 

“Yeah should I get this dry cleaned or do you think they charge too much to remove bodily fluids?” Stiles asks, frowning as he eyes his suit. “And brains, do dry cleaners remove brains Scott?” 

“Dude I have no idea but its worth a dry though right? Its your favorite suit.” 

“I could always have it replicated, we have the money for it, dude that Howell guy was such an ass like really Scott am I stupid?” 

“You’re the smartest guy I know I mean look at you, running like the biggest drug cartel I’ve ever heard of! Like that’s so cool! And I work with you which is even cooler okay. Oh and you’d look so bad ass in a red suit dude, you should get one” 

Stiles nods and smiles at Scott. 

“Do you think you’ll ever get arrested someday?” Asked Scott with a touch of sadness in his voice. 

“Someday but I bet I have mad prison cred already, there’s no way I’ll die in there okay and maybe I’ll meet some sexy guard and we can fuck in the janitors closet or some shit.” Stiles laughs, patting Scotts shoulder. “Not soon though Scotty not soon.” 

*  
Stiles is being fitted for the red suit Scott suggested he get when there’s a knock on the door. He walks over and opens it to see to men in suits standing there.   
“Hello gentlemen what can I do for you?” 

“We’re here for Mr. Stilinski” 

“Right this way,” Stiles leads him to the living room where the man take a seat on the couch while Stiles continues to be fitted for his suit by Allison. “So get talking, what are you here for exactly?”

“We’re well aware of how many trafficking routes you have across the US and we have to say its very impressive considering you’re only 22 and you’re already so successful” 

“You’re so kind but really it’s not complicated, its just logistics and commons sense really,” Stiles smiles at the men knowing who they really are and what they’re really here for. Stiles nods at Allison as he shows him a black tie, winking at her to give a signal that she should take cover.

“Some old man made me clean up after him and what can I say? I’ve made it so I don’t leave any mess behind” Stiles walks to the small cart along the far wall, pouring a drink for himself as he quietly grabs the gun strapped to the bottom of the cart. 

“Now tell me something gentlemen,” Stiles says nursing his drink. “How stupid do you think I am?”

Stiles turns, pointing his gun at the men as the draw their guns as well.   
“You let us in.” One man says.

Stiles snorts, and pulls the trigger quickly killing both of the men. “Ally, get someone to clean this up for me please, I’m going to shower. He slips off his suit and sets it away from the bloody men and strolls to his bathroom.  
*  
Stiles decides he wants to take Scott out to get some drinks for friend reasons and he just wants to spend quality time with his best friend, instead of the brutal things they do almost day to day. The drive to the bar is short since its near where they work. Stiles takes a seat in a far booth with Scott before ordering a couple beers. 

“Hey Stiles why did you decide to do this job in the first place? I’m not saying it was a bad idea but how come?” Scott asks. 

“I needed the money to pay off student loans, and I know you and Isaac didn’t really like where you were working, I mean I guess this isn’t any better…you never had to take this job you know that right?” Stiles looks at Scott with a sad expression on his face, feeling like he had dragged Scott into this when it wasn’t what he wanted. 

“No that’s not…Stiles I love working with you, I get to see you all the time and we get to be bad ass motherfuckers like everyday! And how many people can say that,” He lowers his voice before continuing. “They’re best friends with the biggest drug dealer in the country?” Scott gives him a crooked smile, and Stiles knows that Scott doesn’t regret his choice.

“Yeah,” Stiles smiles. “I guess you’re right Scotty.” Stiles claps Scott on the back, before continuing to sip his beer. 

There are a couple men continuing to stare at Stiles, and to be honest he’s kinda creeped out. 

“Hey Scott can we go? Those guys are creeping me out like hardcore staring at me” Stiles glances at the men who are glaring at him menacingly. 

“Sure” Scott chugs the rest of his beer before walking out to the van with Scott, before the men follow, pushing Stiles and Scott to the ground before on of them knocks Scott unconscious. 

“Scott! Hey get the fuck off me!” Stiles squirms under the man trying his hardest to push him off. He really wishes he had taken up working out, but being a drug lord, he never got around to it. 

“Special Agent Parrish of the FBI, Stiles Stilinksi you’re under arrest.”


	3. Chapter 3

**Notes for the Chapter:**

> ATTENTION: I did rewrites on chapter two on account of one comment suggesting it had been moving too fast (which I also agree with!!) So I have edited it, hoping that it has slowed down some what more than it was but feel free to give it a reread if you like, its not much different from the original, words were changed and things were added or taken out but other than that, that is all!
> 
> UPDATE: 6-24-15   
> This chapter didn't change much from what is was, things were just rewritten, but I will probably redo all of chapter 4 so please be patient! I will try to get it up and posted as quickly as possible.

Out of all the places Derek never thought he would be working at a prison as a correctional officer. Yeah of course its not so bad working there, but it gets annoying and surprisingly fun breaking up all the fights that happen during the day. Once he was searching an inmates bunk and found a shank made from a fucking orange juice bottle! Crazy what the people in prison come up with when they have enough time on their hands.   
Derek is called to the wardens office to be informed of a new inmate that they'll be housing in just a few days.   
"Are you fucking kidding me?! He's being sent here? There are plenty of other facilities in the state he can be sent to!" Derek practically yells into the wardens face.   
"Officer Hale please I am assigning this to you for a reason! You're the best officer we have and I know you'll be able to take care of this guy while he's incarcerated here, and I don't wanna here and bullshit about it you hear me?" Warden Matoi says with an unnerving amount of authority in his voice.  
Derek huffs and walks out of the wardens office, to get someone to clean up one of the max security cells in another sector of the prison. Derek has heard plenty about the Stilinski guy on the news but he never thought someone as powerful as him would be arrested after about 4 years of running the biggest cartel in the US. Out of all the criminals that had to be sent here it had to be him. Fucking hell, Derek really has his work cut out for him.   
*  
Stiles is dressed in a white jumpsuit, before his ankles and wrists are cuffed together, a long chain connecting the cuffs together so he couldn't run even if he tried. He held his head high as he stepped off the bus, then being led by guards into the gates of Hell. Prison, sorry. As soon as the guards lead Stiles past the hallways of cells and the cafeteria full of inmates everyone goes silent as all eyes land on him. Stiles smirks slightly, shuffling forward, an evil smile spreading across his face as the prisoners whisper about who he is and what they know he's done.   
Turns out Stiles does have mad prison cred already. Ha! Scott would love to hear about this! With all the evidence that had been pinned on Stiles (which was actually hardly any, he totally knows how to not leave messes behind okay) his sentence was pretty short, 37 months to be exact. Which gave Stiles plenty of time to get people on his side, and have them working for him was he gets out of here. 

Stiles eyes the juicy guard that's waiting near the entrance to the max security holding cells.

"Oooo" Stiles coos under his breath. Stiles eyes his name tag to see the name Hale etched into it. This Hale man was probably the most attractive person in this shit hole they call a prison. Stiles was sat on the small cot with a thin mattress until his cuffs are unlocked and taken away. Hale stands, getting ready to shut the door as the escorts leave.

"What are you in here for?" Stiles puts on his best bedroom eyes.

"I work here. Obviously" Hale answers, practically grunting. 

"No I mean why is someone as attractive as you working here in this shit hole?" Stiles stands and walks closer to the guard. Officer Hale glares at Stiles before pushing the door shut some more.

"I know you already know my name so tell me yours, might as well since you're already here." Stiles eyes Derek through the bars on the door, biting his lip.   
Derek points to his name tag. “I’m sure you can read Stilinski.” Derek says, a touch of annoyance in his voice, rolling his eyes slightly. 

“Yes Officer Hale, I can read but I’m not big on formality so I like to use first names instead.” Stiles sits on the cot, leaning back against the wall, watching Derek through the bars of the cell door. "So you gotta sit there all day watching me, that’s your job?" 

Derek grits his teeth. "Yes, shouldn’t be too hard watching someone locked in a cell right?” 

Stiles smiles. "Good cause I'm guessing you know how long I'm in for so we're gonna get to know each other just fine. So, do I get some real prison clothes or do I have to wear this," Stiles says pulling on his white jumpsuit. "The whole time I'm in here?" 

"You’ll be issued a new one soon, I’ll go ahead and see if they have one already" Derek mutters before walking away and coming back about 10 minutes later with a navy blue jumpsuit like the other prisoners wear. Derek slides the jumpsuit between the gaps in the bars. Stiles purposely runs his fingers along Derek's as he grabs it and sets it on the cot, beginning to strip. Stiles slips off the laceless shoes the prison issued him, before unzipping the white jumpsuit and pulling it off. 

Stiles feels Derek's eyes on him, probably making sure he doesn’t pull any funny business or something.

"Like what you see Officer?" Stiles says turning toward the door, walking to it, grabbing Derek's hand through the bars. Stiles presses Derek's hand to his chest and moves it down his body, closer to his crotch. Derek's fingers just brush against the waistband of Stiles' boxers before he pulls his hand away and steps away from the cell.

"Just get dressed" Derek says his voice firm but quiet, cock hardening a little in his pants as he think of how soft Stiles' skin was under his fingertips. Stiles gets dressed slowly, knowing Derek is thinking about what happened. 

“Do that again and you’ll be regretting it.” Derek glares at Stiles through the bars, crossing his arms over his chest.

"I'm here anytime you want me...Officer Hale." Stiles says through the bars of the cell. Derek walks away to the bathroom to wait out the growing problem in his pants. 

"I cant believe this guy" Derek whispers to himself before locking the stall behind him.


	4. Chapter 4

**Notes for the Chapter:**

> I will be honest with you guys, I hate the way I wrote this chapter because I literally have no ideas for this fic so if you guys want to suggest ideas for the next few chapters that would be lovely! I'm having a hard time writing lately but I'm doing my best for you guys! 
> 
> UPDATE: 6-24-15
> 
> I have completely redone this chapter because I cant tell you how much I think it sucked now that I looked over but thank you to stateofconstantconfusion for pointing things out to me because if no one had mentioned it I would've left the story as is, but I'm working hard for you guys, I'm looking things up and a bunch of other things to hopefully make my description of prison accurate? I hope that makes sense, I shouldn't get all my ideas of prison from Orange is the new black omg!

Stiles wakes up the next morning, standing up to stretch away the pain in his back from the uncomfortable mattress. He unzips the jumpsuit just enough to lower his boxers and take what feels like a 5 minute piss in the toilet in the corner of the room, where it cant be seen from the door. At least they had a little decency. 

Stiles turns to the sound of someone clearing their throat from the outside of the door. 

“Oh, what a lovely surprise.” Stiles walks over to the door as Derek unlocks it to escort Stiles to breakfast.  
“Yeah, yeah nice to see you too Stilinski” Derek grumbles, voice gruff from sleep.

“Oh, look at that. You remembered my name” Stiles smiles, nudging Derek softly in the shoulder. Derek grips Stiles’ bicep, walking him to the cafeteria. “So Officer Hale what is on the menu this morning?” Stiles asked, a little spring in his step.

“You’ll see when we get there.” Derek glares ahead of him finishing the walk to the cafeteria. Watching Stiles as he’s handed his food, Derek walks over to some of the other guards as Stiles takes a seat with some other prisoners, already sparking up conversation with other prisoners. 

“How’s watching the new guy going?” Officer Mahealani asks Derek, chewing on a granola bar.

“It not all bad but he doesn’t know when to shut up, I don’t know why the warden stuck me with him he doesn’t seem like he needs watch almost 24/7” Derek rubs his face with his hands, before bringing them through his hair, sticking it up. Derek eyes Stiles while he talks to the others, all of them nodding like they’re agreeing to something. Stiles smiles, but it doesn’t mask the evil glint in his eyes.

“You’re very smart so that’s not hard for you to guess Derek, you’re our best officer but you aren’t very…how do I put this, likeable? So I guess you’ll be able to show a little authority or something” Mahealani says, eyeing Derek a little warily like he’s a little scared of his reply. 

Derek just shrugs before going over to Stiles after he finishes his breakfast, and escorts him back to his cell.

*  
“So Derek,” Stiles says before sitting on the cot in the corner of the room.

“Where did you hear that name from?” Derek interrupts, glaring at Stiles angrily. 

“I heard the officer you were talking to say it, and I have to say, I like it.” Stiles leans back against the wall.

“Well you aren’t allowed to call me that so just forget you heard it.” Derek says, locking the door and taking a seat across from Stiles’ cell.   
*  
Derek reads a book while Stiles is asleep in his cell. Derek looks up and rolls his eyes at the position Stiles is laying in, he’s on his stomach, one arm hanging of the edge of the cot, one leg bent at the knee, and his calf propped against the wall. Derek closes his book and sets in on the ground beside his chair. 

“Stilinski!” Derek yells shaking Stiles awake. Stiles scrambles to sit up, but ends up falling off the bed instead. 

“What do you want? I was having a very nice dream okay and you totally just ruined the whole thing. Don’t you have better things to do Derek?” Stiles lays his head back against the edge of his cot. 

Derek covers his mouth a little, rubbing his stubble before standing and unlocking the cell door. “Don't call me that, its time for lunch” 

“Yes! I’m starving, hey do you guys have curly fries? Cause I could probably die from not being able to eat any for the whole time I’m in here” Stiles follows Derek to the cafeteria again for lunch, grabbing his food and sitting at a new table to talk to more prisoners about his plan for them when they get out. 

“So how would you guys like to get some serious cash once you’re out of here?” Stiles asks taking a bite of whatever is on his plate.

The other prisoners eye him warily for a few minutes before agreeing and asking what the whole plan is. 

“Alright, so once you guys get out of here, whenever that is, you’ll call a phone number which I will give you whenever I’m able, and then I’ll arrange for you to be in my business, you’ll make money right away and you’ll have a place to stay, most things you wouldn’t have after people find out you’ve been incarcerated for who knows how long.” Stiles shrugs and smiles a little. “So how about it guys?” 

A man with a scar across his cheek looks around the table then back to Stiles before nodding. Stiles laughs happily. “Great! I look forward to it gentlemen.” Stiles stands and waves Derek over so he can be escorted back to his cell. “I need paper and pencil big guy.” 

“What for?” Derek asks grabbing Stiles’ bicep again. 

“Its classified, Officer” Stiles smiles and steps into his cell. 

“Sure whatever” Derek locks the cell back before sitting and picking up his book.

“Whatcha reading Derek?” 

Derek looks up from his book, looking Stiles in the eye before shrugging. "Don't call me that.."

“Okay man don’t be such a dick about it I’m just trying to spark conversation, while I’m locked in this fucking cell almost all damn day okay?” Stiles crosses his arms and huffs. “Geez” Stiles lays on his bed, facing the wall. 

“Its about the Italian campaign in World War 1” Derek mutters, going back to his book. “What were you talking to those prisoners about?” Derek asks, bookmarking his page.

“Classified” Stiles says turning to face Derek. Derek rolls his eyes before speaking.

“Well if I find out that you’re planning something that has to do with what you do outside of here I might have to report it, its possible whatever it is could extend your sentence.” Derek says leaning his head back against the wall and yawning a little.

“Alright Derek, what I do for my job shouldn’t concern you okay? I have my own reasons and my own methods of doing things and I don’t need to hear shit from someone who works in a fucking prison.” Stiles sneers, sitting up.

“Well look where that shit got you, you’re locked up in this fucking prison for the shit you do out in the real world.” Derek says his voice calm, but Stiles thinks if looks could kill he would’ve been dead the moment Derek looked at him when he first arrived. 

“I got pretty far didn’t I?” Stiles lowers his head to look at his hands. 

“Yeah I guess you did..” Derek mumbles, looking away from Stiles’ sad expression.


	5. Chapter 5

Stiles has only been in prison for a few days and he's kind of already sick of Derek's broody attitude. Like 'Hi my names Derek Hale and I'm the biggest douche on the planet but I make up for it because I'm super duper hot', and Stiles knows that's not how it really works. But sometimes Derek isn't all the bad, one time he even gave Stiles a pudding cup from his lunch before he left to attend to some guard duty stuff. Prison things. 

Stiles grabs the pencil and paper Derek had left for him, and writes down all he names of the other inmates, who could potentially be working for him once they're released. Stiles has made sure that they all get out AFTER him so he can make sure that the people he wants to have on his side will be taken care of properly. He reads through the list, sticking faces to names, and then writing down what each of them had done to get there before crossing out people who he doesn't think would do well in his business. 

There's this one guy who ran away when even approached by a new person, and he's only in prison for something that wasn't even his fault. But anyway, Stiles is almost confident that he has a substantial list of people who would be great assets to what he's working for, and if they aren't then he has no problem taking care of them. 

Stiles unzips his jumpsuit revealing a white t-shirt underneath before tying the sleeves of the jumpsuit around his waist. He paces around his small cell, taping the eraser side of the pencil to his bottom lip. He grabs the paper before jotting down some quick notes in hardly eligible handwriting. Stiles thinks fast so he needs to write quickly before the thought disappears. He looks down to his notes, his eyes widening at what he's written.

'Officer Hale can suck my dick!!' 

"What the fuck.." Stiles chuckles before scribbling it out. 

"What's the deal?" Stiles hears behind him. He turns to see Derek standing there, with two books in his hand. 

"Uh nothing! Nothing at all just uh thinking is all, I mean not that its any of your concern what I think about, not that you'd actually wonder what I think about its just that uhm-whats in your hands?" Stiles shuts his mouth quickly before he rambles on, trying not to give anything away, but the look on his face isn't helping. 

"I brought a book for you so maybe you wouldn't talk so much." Derek deadpans before handing the book to Stiles and taking his regular seat across from the cell door. Stiles takes the book from Derek and sits on his cot, reading the summary. 

"This sounds like a good book, why did you pick this one?" Stiles asks, looking back up at Derek.

"Its one of my favorites, thought you might like it." Derek presses his lips together before looking down at his book.

Stiles smiles a little as he opens to the first page and begins reading. 

"Hey Derek, what's your favorite thing about this job?" Stiles asks, not taking his eyes off the book. 

"Once I found a shank made from an orange juice bottle, so that was interesting." Derek shrugs. "Its almost time for dinner"

"Yeah okay..this book isn't actually bad but this Maria character sucks ass, she's such a bitch okay, whens the last time she got laid? Maybe if she got laid she wouldn't be so grouchy. Hey Derek do you think if you got laid you wouldn't be so grouchy?" 

Derek chokes on air at the question, coughing as his face turns pink.

"I'm not grouchy, you're just annoying, do you ever stop talking?" Derek crosses his arms.

"I'm not annoying okay you just cant keep up with my quick wit and amazing charm," Stiles shrugs smiling. "Hey! Is dropping the soap a real thing? Like does that actually happen?" 

"Oh my god." Derek lets out in an irritated whisper. 

"Derek you should know these things, you work here! It must be a crazy everyday thing! Do guards have sex with inmates? Is that a thing too, no wait you could lose your job if they found out right? Man that sucks, like some shitty romance novel written by someone who doesn't know shit about love."

"Stiles shut up" Derek is trying hard to cover up his smile. 

"No okay look at it this way like--hey you used my name." Stiles looks at Derek, his whiskey colored eyes reflecting the luminescence of the fluorescent light bulbs in the ceiling.

"Is that a problem?" 

"Oh so you can use my name but I cant use yours?" Stiles crosses his arms before raising his thin eyebrows at Derek.

"You already do use my name?" Derek says a little confused, raising his eyebrows back at Stiles. 

"Good point anyway, I'm hungry so can we go now?" Stiles asks, walking to the door. 

"In about ten minutes we can" Derek goes back to reading his book.

Stiles sits on his cot, covering his face with the book as he smiles to himself, because he totally got Derek I'm grumpy as fuck Hale to smile, so. They're getting somewhere.

*  
At dinner Stiles finds more people for his list, occasionally glancing at Derek, watching him talk to a guard with perfectly tan skin and big brown eyes. Stiles squints, trying to get a read on what his name tag says bit its just a little too far away. Stiles stands up and people around him still cower and shy away when he steps near them, but its not really about who he is, its just about the way the media has portrayed him. 

Okay well that's not really true, Stiles has done some pretty shitty things since he was 19 but he doesn't regret them because he was just trying to make a good life for himself and his friends and this is where he's ended up. But he doesn't regret any of it, he did everything for a reason and its gotten him far in life. Who knows where he would be now if he had stayed at that shitty dead end job at the hardware store? He did good for himself. 

Derek walks over and Stiles just doesn't say anything when Derek takes him back to his cell. Stiles lays down on his cot, facing Derek. 

"Do you ever get tired of your job Derek?" 

"Sometimes but its not bad, some prisoners here are actually really nice believe it or not." 

Stiles nods before turning so he's facing the wall. 

"Why is something bothering you?" Derek asks sounding a little concerned. 

"No I'm just tired that's all..I'll see you tomorrow" Stiles closes his eyes but he doesn't get much sleep that night. 

*  
Its not that Derek doesn't like watching Stiles, or that its hard, its just that its so easy to be around him, he can talk about anything and everything, its almost ridiculous. It feels like its almost too easy, the warden placing him on this job still doesn't make any sense to him but he's kind of enjoying his time with Stiles, even if he is locked behind bars. 

Stiles might actually like spending time with Derek. Sure he doesn't talk much but he's not a complete shut-in either, and Stiles is grateful that he actually has someone who is somewhat nice to talk to all day. Derek's not a bad person, Stiles can tell, maybe its just the prison environment that keeps him quiet. And Stiles can even say Derek has nice taste in literature. 

*  
Stiles is sitting at a table, eating quietly until one of the prisoners starts yelling at a guard, then more people join in, agreeing with the man about how this prison is shit and the guards don't do anything but sit on their asses all day. Soon the whole cafeteria is practically rioting, people start throwing punches and food, pulling out makeshift weapons from their jumpsuits. 

Stiles pushes himself up quickly, avoiding the major fights, stepping away from someone who comes at him with some sharp thing made from who knows what, Stiles pushes the man away, but he comes back at him again, swinging the weapon, cutting Stiles across the cheek. Stiles grabs the mans arm and uses his free hand to slam on the mans back, pushing him to the ground, before moving his arm in such a way, that it snaps his collar bone. 

Stiles stands up quickly walking back towards where his cell is before he's grabbed by the arm by a guard. 

"Get off me!" Stiles yells, trying to tear his arm away only to realize that its Derek who's gripping his arm, looking at him with a worried expression eyeing his cheek. Stiles pulls his arm away before walking back to his cell before one of the other guards throws a bottle of tear gas into the middle of the riot. 

Stiles sits on his cot, before Derek kneels in front of him, gently grabbing his chin, turning his head to get a look at the gash on Stiles' cheek. 

"I'm fine.." Stiles pulls his head away, looking away from Derek. 

"You were cut across the face! Stay here I'll go get a first aid kit okay?" Derek purses his lips, looking at Stiles. Stiles gives him a small nod before Derek leaves, coming back a few minutes later with a first aid kit in his hands. He kneels between Stiles' legs, wetting a small cloth with some antiseptic cleaner before gently dabbing his cheek with it. 

"Ow fuck!" Stiles pushes Derek's hand away, waiting for the sting in his cheek to subside. 

"I'm trying to help, let me clean it or it will get infected." Derek glares at him before Stiles gives in, nodding again before Derek takes his chin in his hand again, dabbing at the wound. Stiles shuts his eyes, reaching up a hand to grip at Derek's arm, while the burning gets worse in his cheek as Derek continues to clean it. 

"Its not bad enough for stitches but it will leave a small scar." Derek says, using his free hand that Stiles isn't gripping to open up some cream, rubbing it on the wound so it wont get infected. 

"Thanks.." Stiles squeezes Derek's arm once more before dropping is hand so Derek can bandage the cut. Derek nods, cutting a strip of gauze and medical tape to cover the wound. 

"No problem.." Derek says quietly. Derek is so close to Stiles' face he can feel Derek breathing shallowly as he finishes up. 

"It doesn't hurt anymore so you must be pretty good at this kind of stuff." Stiles mumbles, breath ghosting across Derek' cheek.

"My sister used to scrape her knees and stuff all the time so.." Derek says before pulling away and putting stuff back into the first aid box. Derek stands and starts walking away before Stiles reaches out and grabs his hand. Stiles looks up at Derek with those almond shaped, amber eyes before smiling a little. 

"No really.. thank you Derek." 

Stiles drops his hand but not before Derek gives it a light squeeze, returning the small smile.


	6. Chapter 6

"Hey Derek you think they'll let me out early for good behavior?" Stiles asks, sitting up, peeling off the bandage from his cheek so Derek can replace it. 

"You just broke a guys collar bone so no maybe not" Derek eyes him and the cut on his cheek. 

"Yeah but in my case it was self defense I mean, he did cut me with, something I don't know what it was made from. But! Buuuut, I did good, you should've heard that bone crack Derek it was insane, I could feel it in his back" Stiles muses, with a dreamy look on his face while Derek gets a fresh bandage ready. 

Derek just shakes his head and rubs some more cream on Stiles' cut. "I guess you do that a lot?" Derek asks, unrolling some medical tape.

"You wouldn't believe me if I told you Officer," Stiles smirks at Derek. "Lets skip a bandage today please, my face feels weird wearing one, I wanna air it out or whatever, hey can we skip lunch today? I just kinda wanna hang out with you, if that's a thing I can do, cause I like talking to you, even if you are like my baby sitter sort of, not that I need a baby sitter cause I'm 22 so yeah.." 

"Sure we can do that" Derek gives him a small smile before wiping his hand of first aid cream. Stiles grins at Derek, and grabs his hand gently. 

"I've been here a few weeks already and you've never really smiled before, and you don't get offended by the things I talk about and its nice to know I have at least one friend in here." 

Derek looks down at their hands, before Stiles links their fingers together. "I like you Derek." Stiles gives his hand a squeeze. "But can I take a shower? I feel rank." 

"Sure I'll take you." Derek stands, pulling his hand away just as they step out of Stiles' cell, leading him to the showers. Stiles looks around and there's no one in the showers which is awesome! Cause he doesn't really want other people to see him naked, even though he's totally super confident about his body. Maybe its because lots of people in this prison have tattoos and Stiles doesn't have one. Natta. 

"Hey Derek," Stiles turns and leans against the small door that covers from his waist down. "You got any tattoos?" Stiles asks, propping his head against his hand and smiling a little. Derek faces him and crosses his arms before answering. 

"One." 

"Where at?" 

"My back, between my shoulder blades." 

"Can I see it?" 

"Nope." 

"C'mon please?" 

"No, finish your shower..please. And don't drop the soap." Derek turns back around, while Stiles chuckles a little to himself. Derek cant help but turn around and peek at Stiles a little, catching a glimpse of his ass. Derek stares for a few seconds, noticing how round and supple it looks. He's still staring at Stiles' backside when he turns the water off and grabs his towel, drying himself off. 

"What? Is there something on me?" 

"N-no I just uh..no" 

Stiles smirks, wrapping the towel around his waist. "If you were staring just say so.. I kinda don't..really mind, you can look at me..if you want." Stiles grips his towel tighter then nods quickly locking himself in a stall to get dressed. Stiles sits on the toilet, contemplating about what he should do when he's hanging out with Derek. Its just for a few hours so it shouldn't be too hard, he hangs out with Derek like everyday! Well it is kinda Derek's job to look after him, which still doesn't really make sense to either one of them but they're getting along so its okay. Stiles really likes spending time with Derek. 

Stiles steps out of the stall after he gets dressed and walks over to Derek, entirely sure his face is red. "If it means anything I'd look at you if you were naked too" Stiles says, wringing the sleeve of his jumpsuit. 

Derek just stops and faces Stiles, his eyes a little wide and he looks kinda tense. "You have a nice ass" Derek says, then looks away, looking around eyes landing on anything and everything, except Stiles' face. 

"I bet your ass is nice too, you'll have to show me sometime" Stiles grins and waggles his eyebrows, lightly nudging Derek's shoulder before walking to his cell, Derek following behind, absolutely stunned. Stiles takes a seat on his cot, gesturing Derek over to take a seat next to him. Derek sits, leaning his back against the wall. 

"So I was thinking that, I like hanging out with you and stuff even if it's your job to look after me and besides, you're the coolest guard man." Stiles nods, trying to emphasize his point. 

"You're one of the nice prisoners I told you about, top five. and I like hanging out with you too, despite my job." 

"Tell me a story." Stiles scoots closer to Derek, letting their shoulders touch. 

"About?" Derek looks ahead of him at the open cell door. 

"Your prison job, tell me a funny story or something and I'll tell you one about my job" 

"Okay so every so often we get new prisoners and we have to do strip searches, and they were all these really intimidating men, there was this one guy who was huge and I mean he looked like the fucking Hulk, so one of the guards was like 'Bend over and spread 'em', and everyone except Hulk guy did was he said and then in the highest pitch voice you can imagine," Derek tried to stifle his laugh before continuing again. "He says 'SAY WHAT?! My chick don't even see my asshole why you got to?!' I swear it was the funniest shit I had ever heard during one of those things." 

Stiles is practically howling, Derek even made his voice higher to imitate the man and it was just hilarious. "Dude its so funny seeing you talk like that, oh my god, you're usually like 'Hi my name's Derek Hale and I'm super grumpy and broody bleh' but you're actually super cool fucking Christ" 

"Okay," Derek says, calming down. "Your turn." Stiles nods before thinking for a second. 

"I was 19 when I got into the drug business believe it or not, and I think the first time I ever tried a drug was a few months after I started, and my friend Scott convinced me to try acid and I was like 'what the heck' and I did it, and after about 30 minutes I started feeling it and Scott looks over at me and he goes 'I dare you to get on top of your car and do a strip tease.' So after school got out I climbed on top of my Jeep and Scot turned on some seductive song and I started to strip in front of every one it was ridiculous and someone took a video of me and posted it online and when I went back to work all my workers kept hounding me about it, and even imitated me and it was the funniest thing I had ever done, but of course I never did drugs again" Stiles shrugs sheepishly, looking at Derek. 

Derek just swallows nervously, looking back at Stiles. "Your eyes are really pretty.." Derek mutters glancing down at Stiles' mouth, thinking about how those lips would feel on his, or how good they'd look wrapped around his cock. Derek doesn't realize what's happening until its a little too late, but Stiles is leaning closer, lightly pressing his lips to Derek's. He takes a second but he presses his lips back, pulling Stiles closer. 

Stiles rests a hand on Derek's thigh, before Derek settles his hand on Stiles' neck deepening the kiss, their lips moving perfectly together. Stiles is really getting into it, stroking Derek's thigh before Derek abruptly pulls away and moves Stiles' hand from his leg. 

"I cant..I cant do this.." 

"You seemed pretty into it.. pretty into me" Stiles bites his lip, looking down at his hand, gripping the blanket. 

"No I mean we cant do this, I could loose my job and you're-- you're in here," Derek gets up sighing like he's a little irritated. "I cant do this I'm sorry.." 

"But I like you, I thought you liked me too and you kissed me back!" Stiles stands, reaching for Derek's hand. Derek steps away. 

"I do like you and that's why I cant do this, if anyone found out I would get fired and you could be in here longer or something I cant do that to you.." Derek looks up at Stiles before sighing again, tearing his gaze away from Stiles' face, with a broken expression. 

"Sorry..Sorry I kissed you, but I'm not sorry that I like you Derek." Stiles sits back on his cot, looking down at the ground. "If I weren't in here, but you knew who I was would you still want to be with me?" 

"Yes, I would..I don't care about what you do outside of here, but in here I cant--" Derek tries. 

"There's no difference except that I'm locked up in here! Its not really my fault, okay maybe it is, but if you really liked me that wouldn't matter.. shouldn't matter.." Stiles looks up at Derek and Derek looks truly confused before his face softens and he looks back at Stiles before sitting back down beside him, grabbing his hand. 

"I can keep a secret if you can.." Derek says, linking their fingers together.

"I don't know about you Officer Hale but I am very great at keeping secrets." Stiles grins before Derek leans in, planting another kiss on his lips. 

"I can keep them too." Derek smirks.


	7. Chapter 7

**Notes for the Chapter:**

> I would like to thank stateofconstantconfusion for giving me some lovely ideas for this chapter and ones to come! Thank you so much, everyone for all your comments and things, it really means a lot to me! :)
> 
> (Also there is some form of sexual harassment and attempted murder so if that's something that bothers you please be cautious)

Prison wasn't entirely bad. There were nice people and even if the food wasn't any good Stiles and Derek had each other and that's what mattered most to Stiles while he was locked up. Today was a big day because Scott was finally coming to visit, a month after Stiles had been arrested. But almost as soon as he wakes up his day goes to complete shit. 

"Stiles we really need to talk, like right now." Derek was standing on the other side of Stiles' cell door, which wasn't exactly normal based off the daily routine that's happened the past two weeks since Stiles and Derek had started their relationship. Derek looked almost confused and hurt, his eyes looking everywhere but at Stiles' face, and to be honest it was making Stiles anxious. Derek always unlocked the door and stepped inside taking a seat by Stiles, planting a soft kiss to his cheek. 

"What's going on? Is everything okay?" Stiles walks to the door, reaching out to take Derek's hand in an attempt to calm him down, but Derek just stepped backwards, kind of cringing when Stiles had reached out to him. 

"I can't do this anymore, I cant be with you. Not like this." Derek looked Stiles right in the eyes, his face taking on its usual broody scowl. 

"You're breaking up with me? Why, did I do something to upset you?" Stiles' eyes searched Derek's face for any sign as to what was happening in this moment right now, but he couldn't find anything. Derek's face was emotionless and stale. 

"I don't think you really understand what I'm risking keeping this," Derek gestures between Stiles and himself. "A secret, I could lose my job and go to prison. I cant do anything with you while you're locked up in here. When we kissed I was caught up in the moment but we cant be together anymore." 

Stiles stands behind the bars, stunned, but oddly more upset than he should be since they weren't together for very long. "Okay, I get it." Is all Stiles says before nodding and going back to his cot and laying down to face the wall. If Derek wanted to be emotionless then Stiles could play that game too. 

*  
The visit with Scott goes well, despite Stiles' shitty attitude. He's discussing things with his colleague Lydia, who also happens to be his excellent lawyer. 

Stiles keeps his voice to a whisper when he talks to Scott and Lydia about potential employees. He props one leg on top of the other slowly pulling out the list he's been keeping for the month and a half he's been in prison. The booths the phones are connected to have a slight gap in the bottom where the desk part connects to the legs that hold the entire thing up. He sweeps his eyes down, hinting that he's slipping something under and begins to speak once Lydia grabs the list and opens it.

"I've been speaking with other inmates and I compiled a list of potential workers that are being released after I am, now I want you to search everyone who isn't crossed out and print out each background you find. Previous jobs and residence, their permanent record, things like that and let me know everything." 

Lydia and Scott nod before Lydia stashes the list and pulls out multiple files before she speaks. "I have talked with lost of people to get this organized and approved and I've had professionals come in and examine all the evidence that had been pinned on you. I helped them make connections that proved you really had no serious involvement in many things before they finally agreed and I took it to the judge that had finalized your sentence and--" Lydia is interrupted when Scott snatches the phone and finishes her sentence for her. 

"We got at least 20 months taken off your sentence!!" Scott grins, crooked. 

"Seriously?!" Stiles jumps out of his seat, getting yelled at by a guard to sit back down. "That's amazing I cant believe that you went through all that trouble for me, that means I only have about 15 months left to serve and I'm out of here?" Stiles takes his seat, grinning widely, his bad mood swept away by such great news. He always knew Lydia would come through for him and she did a great job. 

"Yes, and we'll be waiting for you when you get out with that red suit you have yet to wear!" Lydia smiles, probably because she knows she's a boss ass bitch and she had to go through more than necessary to get his time shortened by such a great amount. But she knows all of what she proved was absolutely true, and Stiles was hardly involved in anything that had been pinned on him. 

*  
After Scott and Lydia had left Stiles sat in the seat a moment longer, a small smile on his face. His business was still doing amazing and he was getting out way sooner than anticipated. Stiles is sitting on his cot, back leaned against the wall, legs crossed in front of him as he writes some new business ideas to get more product distributed, and new ways to collect money, but mostly, he's sketching himself in that amazing suit he has yet to wear. Stiles flips the page, starting to sketch something new but stopping when the face is complete. 

It's Derek's face. He drew Derek's face. Derek, the guy who broke up with him and hadn't shown up for the rest of the day, leaving Stiles alone in his cell. Stiles throws the notepad across the room before laying down and curling up on his cot. He's facing the wall when someone slips something through the bars and drops it on the floor. By the time Stiles turns around to see who it was the person has disappeared, leaving a brown paper bag on the floor. 

Stiles moves over and plucks it from the floor, opening it up to find some things that Derek used to sneak him for lunch. There's a sandwich, two whole oranges, (Stiles' favorite) and a pudding cup along with something to drink. Stiles smiles a little appreciating that Derek had at least some decency to feed him instead of avoiding him completely. 

*  
Derek has been avoiding Stiles all day since their breakup and he's trying to bribe Erica into switching positions with him so Derek doesn't do something stupid. 

"Why do you want me to take your job?" Erica asks, munching on a salad she'd brought for lunch. Derek groans as he pours a cup of coffee and takes a seat across from her, thankful they're the only ones in the break room. 

"Because I asked you to?" Derek deadpans. 

"No seriously why? Did you guys fight or something? Just yesterday you wouldn't shut up about him. So, what happened?"

Derek sighs before blurting it out. "I like him and I don't want to lose my job." 

Erica's face breaks into a big smile. "Boyd owes me $20 because I fucking knew it! Derek has a crush! You guys would be soooo cute together and you know it." 

"That's the point Erica," Derek drops his voice to a whisper. "We tried dating and it was good for a while but I can't do it, not while he's locked up in here...and I'm risking a whole lot trying to keep it a secret. So if you could please help me out here..I feel like he might be using me to get on people's good sides..he's been making some dumb list and--" 

"Derek, I'm telling you this because I love you. No I'm not switching places, but I will keep your secret and help you get in his pants and also I seriously doubt he would use you that way, despite his actual career... Now go figure out what you're gonna say to him and then go tell him!" Erica stands and walks from the room, her blonde curls in a ponytail swishing from side to side as he walks away. 

Derek already knows he isn't going to say anything, because he has no idea what and also, he's afraid. Not afraid of Stiles, but a little afraid if he tried with him again he might regret it. Sure he'll still do his job, he'll just avoid talking to Stiles about anything and probably almost everything because Derek sucks at using words and everyone knows so. 

*  
Stiles doesn't really mind being by himself for the few days that Derek doesn't show up, but a different guard swings by and escorts Stiles to the showers (which he really needs). He's still bothered by the fact that Derek's been ignoring him, but at the same time he doesn't mind because his mind is too focused on how many other people there are in the showering room with him. When Derek brought him here they were the only ones in the entire room which was amazing. 

Stiles undresses and sets his clothes in the usual spot before starting a shower and stepping in, trying to ignore the other inmates staring and snickering at him. He's trying to go faster than he usually does, a little self conscious with all the other men staring at him and right now he really wants to admit that the only man he wants staring at him is Derek. But Derek isn't here watching him like he usually does, and the guard who brought him here doesn't seem to care about making sure Stiles is watched over. 

Stiles turns around, back facing the wall to wash the shampoo from his hair and to keep watch to make sure no one tries anything until a huge man comes up to him, and Stiles tries really hard not to snicker, remembering the story Derek had told him a few weeks ago. Stiles tries to walk around the man, to grab his towel until he's shoved back violently against the wall. He lets out a groan as the man comes closer pinning him against the wall, where various tiles are broken and there's a sharp piece poking Stiles in his back beneath his shoulder blade. 

"C'mon man I just wanna get out of here." Stiles tries to push the man away, but this man is much larger and stronger than he is so all his efforts go to waste. 

"You aren't going anywhere." The man growls, glancing back at the guard who gives the man what seems to be a go ahead nod, before turning away and stepping out of the room. Stiles turns his head, not wanting to look at the man, as he presses Stiles' body harder to the wall, the sharp tile piece breaking skin. The man grabs Stiles' ass, fairly hard, before grabbing his neck with his free hand with the same strong grip as the other. The mans hand tightens around Stiles neck, nearly closing off his windpipe and Stiles is sure there will be a harsh hand shaped bruise there in the morning. 

Stiles squirms, trying to get free of the mans grip but he only succeeds in making the tile cut deeper into his back, the man pushing Stiles down to the ground and onto his knees. Stiles lets out a voiceless scream as the tile slices through his skin, the gash going from the middle of his back all the way up to near the back of his neck. The man lets go and walks away leaving Stiles gasping for air and watching his blood mix with water as it flows down the drain. 

*  
The pain in his shoulder is excruciating, Stiles just lies on his bed, no shirt on facing the wall as the gash throbs, still bleeding profusely. Stiles' white undershirt had been soaked through with blood as he tried to keep pressure on what he could reach but it just wouldn't stop bleeding. He was close to passing out from the lack of food, because no one had been by his cell to bring food or give him medical assistance no matter how much he pleaded. He realized it was useless since he was in another building entirely and he'd given up, his voice too raw and exhausted to continue. 

"Stiles?" A familiar voice says on the other side of the cell door. 

Stiles tries his best to turn and see who it is, but he lets out a whimper from the pain in his shoulder, dropping the blood soaked t-shirt to the floor, exposing the long deep gash on his back. 

"Oh my god don't move I'm coming in and I'm gonna get you some help, oh god I'm so sorry I shouldn't have left you." The voice rambles on as he's hoisted up and taken to the infirmary, body limp in the arms holding him. Stiles passes out to the voice yelling his name, trying to shake him awake. 

*  
Stiles wakes upon his side with an aching pain in his back and neck. He looks around not realizing where he is until his eyes land on a familiar face sitting in the chair next to his bed. 

"D'rk.." Stiles tries but his throat is too raw from the choking and all the yelling he had done before. 

"You're awake, I was so worried, what happened to you?" Derek asks, worry etched all over his face. 

Stiles tries his hardest to speak but Derek just shuts him up by handing him a note pad waiting for Stiles to write out what had happened to him in the shower.

"Stiles I'm sorry.. If I hadn't left you alone..--" 

"S' okay Der.." Stiles says weakly reaching to give Derek's hand a small squeeze. Stiles gives a small smile when Derek doesn't pull away, but he doesn't react any other way either and it doesn't bother him once bit. 

"Stiles I," Derek looks down at their hands before he links their fingers together. 

"S' okay.. I like you too but I understand why you broke up with me," Stiles takes a deep breath wheezing as he does so. "But I got 20 months taken off my sentence and maybe if you still like me...we can try again? When I'm not here." Stiles gestures around the room, talking about the whole prison thing, voice hoarse and weak but he knows Derek heard every word. 

Derek doesn't answer but he presses a quick kiss to Stiles' forehead before leaving the room and Stiles, alone with his thoughts.


	8. Chapter 8

**Notes for the Chapter:**

> I almost forgot to mention that I will be traveling to Iowa for most of July to earn some money, I am leaving this week on the 2nd and should be back near the 23rd or 24th, so if I don't update during that time I am very sorry, but once I return I will put out a new chapter or two to make up for the time I was gone!
> 
> Thank you again for all your comments and things, I love reading them. It means a lot to me to know you guys like my work!! :)
> 
> EDIT: 7-1-15  
> There has been a few things that have been changed in this chapter! So thank you stateofconstantconfusion for helping me out with this!!   
> Also I still have no idea how long I will be working for this month so I really have no idea when the next update for this chapter will be uploaded but as soon as I come up with ideas for it and get the chance to write it I will upload it! Thank you all for being patient with me!   
> In the mean time I have other short stories I had written that I'll upload when I get the chance to, sort of as a filler for the fact that I can't update this story right now!

Stiles ended up staying in the infirmary for about a week before he was released back to his cell, where he continued to rest. During this time he spend most of his time lying on his stomach He , as to not aggravate his still healing back. He hasn't spoken since the day Derek had left, giving his throat a much needed rest.

Stiles pushed himself up slowly, grabbing his notepad to finish the sketch of Derek he had started a week before. It was a little difficult, not using his left hand to avoid putting strain on the gash on his back. The wound had been stitched up and cleaned regularly, and as long as he didn't move his left arm too much it didn't hurt too badly.

Stiles had almost finished sketching Derek's torso when he looked up to see Derek standing on the other side of his cell, looking right at him. He gave Derek a small smile, before going back to his sketch, which wasn't turning out as bad as he thought it would.

"I wanted to see how you were doing, I heard you got back today." Derek said, taking his usual seat that had been empty for far too long. Stiles flipped the page and wrote that he was feeling alright but that he hadn't spoken since the attack because of his throat. 

Derek nodded a little before handing the notepad back and continuing.

"I'm sorry about what happened to you but I promise I'll stay with you from now on okay? I'm sorry I left before." Derek said, but his words were rushed, like he had to get them out or he would burst. Stiles felt like Derek didn't really mean what he was saying, he just looked at Derek, a little confused before opening his mouth and closing it again, not knowing what to say.

"We can't be together Stiles...I need you to know that." Derek leaned back in his chair, looking at Stiles waiting for a reply. Stiles nodded and gave another small smile, showing that he understood what Derek was saying. Stiles got the feeling that Derek meant they couldn't be together, ever, even when Stiles was released and it tore Stiles up inside to know that after everything, Derek didn't want what Stiles so desperately wanted.

He didn't let his face show any sign that he was upset by Derek's words, so he just sat back on his cot and finished the sketch within 10 minutes. When he was done he stared at it, ripping it out and shoving it under his pillow.

*  
Derek leaves feeling disheartened, he hated rejecting Stiles but there is no future if they are together in here. There is too much risk. All he can do is hope that there is a future for them after this. 

 

He goes to eat lunch with Erica.

"I have an ideaaa" Erica cheered gleefully before sitting in front of Derek.

"About what?"

"How you can win him over when he gets out of here duh!" Erica settled in her seat, twirling her hair around a finger. Derek eyes her skeptically because usually her ideas were usually pretty awful but he couldn't help but listen to her whenever she came up with a new one.

"Well?" Derek asks, staring at Erica expectantly.

"When he gets released, you go after him and kiss him as soon as he steps outside!! It’s a great idea, Boyd and I came up with it. Whatcha think?"

"That actually isn’t a terrible idea, but what if I’ve lost my chance by then?"

"He’s worth the risk right? You'll never know if you just let him just walk away. You could never see him again and then he'd be that one that got away and you'd be mourning over what could’ve been the rest of your life. I say you should go for it." Erica nodded and pushed herself up from her seat before smirking at Derek and leaving.

*  
Stiles wasn't lonely anymore. Derek was there all day everyday now, and even though Stiles was back to talking he seldom spoke around Derek. He wasn’t sure what had changed, before he had loved talking to Derek. Stiles was still hurt by Derek rejecting him, it felt like something had changed and he wasn’t sure if he could get back what they had. He wasn’t sure if he wanted to. The months went by and Stiles barely spoke to Derek.

The only thing spoken was as occasional thank you when Derek cleaned Stiles' wound or brought him some more fruit. Stiles was aching to tell Derek how he really felt, especially now that he was getting out sooner than he'd expected. He could always contact Derek after he's gone if he wanted to. He almost told him a hundred times but every time all he could think of was that Derek doesn't want anything to do with him, and would reject him all over again.

"I know you don't want to be here," Stiles says, not looking up from a book Derek had brought him.

"Sorry, what?"

"Here, watching me I know you don't want to be stuck here." Stiles says looking up from his book to see Derek staring at him with a confused look on his face.

"I dont mind watching you at all" Derek says, sounding genuinely confused.

"We hardly talk anymore, but I know you still care about me." Stiles says raising his eyebrows at Derek and crosses his arms. "But you wont talk about it, you still avoid me, you hardly even look at me Derek, I know how you feel about me."

"How do you--"

"Erica told me." Stiles says, hating the way it comes out of his mouth, spiteful and childish sounding. It sounds like he doesn't feel the same about Derek, when really Derek is all he thinks about.

"Dammit.." Derek whispers to himself, vowing to rip Erica a new one when he sees her.

"Its okay Derek, I get that you don't want to be with me and that's fine, okay? I understand but that doesn't mean you should ignore me because you're too scared to talk about your feelings for me. I hate that you think that we can’t ever be together all because I was locked up in here or whatever. I'm sorry okay? This situation sucks ass and it sucks that I can't be with you and I hate it okay?" Stiles looks away from Derek and faces the wall, not really wanting to look at his face.

"Stiles I--"

"Don't." Stiles says sternly, closing his eyes trying to fall asleep.

*  
Derek is still stunned by what Stiles had said. Did he really believe that Derek didn't want to be with him once he was released? Derek would probably give anything to be with Stiles since he realized how he'd felt about the other man. Derek hadn't had any luck with relationships in the past but he had a feeling it would be different with Stiles.

Derek actually can't wait for Stiles to get out of here. Can't wait to show him how he really feels, but at this moment he can't even tell him because he's so afraid of losing his job or worse. Derek leaves Stiles a bag of fruit before leaving for the night.

Derek wakes in the morning and gets ready before heading to work lost in his thoughts the whole time. He went to go change Stiles bandage waking him by opening the first aid kit.

"Sorry about yesterday," Stiles says as he pulls of his shirt to give Derek access to his back. Stiles sits on the floor to make it easier for him..

"It's okay...your back is healing nicely, soon I won’t have to clean it anymore." Derek says, a tinge of sadness in his voice.

Stiles turns around to face Derek, looking him in the eye. "No its not.. Derek..I just want to touch you.. all the time and I can’t do that-" Stiles stops speaking when he notices Derek leaning in closer to him.

Stiles wants nothing more than to be able to kiss him anytime he wants, he knows that Derek likes him too and doesn’t want to spend any more time not being with him. He wishes that Derek could see what he was missing. Not just the physical but seeing who he really is outside of these walls. He decides to show Derek what he’s missing. Before he could do anything Derek closes the gap.

"Screw it.." Derek whispers right before his lips meet with Stiles'. The kiss is soft and slow and it conveys everything Derek wants Stiles to know. Stiles slides his hands up, cupping Derek's neck, his long nimble fingers reaching into the back of Derek's hair.

Stiles pulls away breathless, eyes scanning Derek's face. "Derek..."

Derek looks both pleased and guilty.”Stiles...we can’t…I thought I could..but I can't.." 

Stiles pauses. He knows that Derek likes him but every time they start to go anywhere Derek freaks out. He is so done with this.

“I know you like me and yet every time anything happens you freak out and I can’t figure it out. Why? Is it your job? Honestly is it that much more important than me? Is it because I’m a criminal? Am I not worth your time? What? Do you have anything to say?”

Derek is caught off guard by the word vomit that just happened, his brain trying frantically to catch up. He looks at Stiles with a blank expression.

Stiles, thinking he isn’t going to get an answer storms away to the court yard leaving, Derek dazed and confused. Not knowing exactly what happened.

I want to be with you, even if it scares me, I don't care. You’re worth it." Derek says even though there isn’t anyone to hear.


	9. Chapter 9

**Notes for the Chapter:**

> I know this chapter is probably shorter than the others but I'm planning to end the story soon anyways so here we go! 
> 
> Thanks again to stateofconstantconfusion for helping me with this chapter!

Stiles needed time to think. He knew that he and Derek would be great together but he needed to move things along. He knew he had a card up his sleeve but didn't know if this was the right time to use it. 

“Fuck it." he thought to himself.

Stiles knew that Derek had every other weekend off. He always missed seeing Derek at those times but was glad to see other people once and a while. His two closest friends in the prison (if they could even be called that) were Erica and Danny. Erica terrified him and made him want to worship at her feet. Stiles hopes that Erica and Lydia never meet, because that would be..terrifying to say the least. But of course, it probably wouldn't happen, considering who they both were and what they did. The other was Danny. Stiles would never say anything but he and Danny went way back. They grew up in the same town and their mothers were good friends. Needless to day they spent a good amount of time together in their formative years. Danny moved away during high school and they fell out of touch. During his time in prison he and Danny had reconnected a little. Stiles was surprised to find out that Danny had a degree in computer sciences and was pretty good at getting information that wasn't available. 

“Danny my man” Stiles exclaimed “good to see you again!”

“Mhm” Danny said sleepily. 

“Ooh were you out late last night? Did you have a gooood time?” Stiles asked with a wink and a sly smile. 

Danny was clearly not in the mood to talk about his late night affairs, it was too early and he had stayed out too late. But he'd met a good guy, Ethan, and couldn't say no. 

“Oh, I know that look, tell me about him” Stiles said waggling his slim eyebrows. 

“Only if you never do that again.” Danny figured most people wouldn’t talk with an inmate about this but he had known Stiles a really long time. Stiles had really saved his ass a couple of times in the past. And if sometimes Stiles needed him to do a little ‘digging’ into someone...well it made vacations come a little more often. 

"You know if you ever want to make some real money you should get out of the guard business. I could find a place for you." 

"Thanks, but no thanks. I'll stick to this."

"Let me know if it changes, surely this job can't be so bad but you know, the offer always stands for you." Stiles said with a secretive smile. He knew eventually Danny would give in and come work for Stiles full time, instead of occasionally. "So...Derek, tell me about him. Please, it's like talking to a brick wall sometimes."

Danny wasn't stupid. He knew there was something there. Stiles and Derek seem fit together in a weird way. A good way. Stiles was the yin to Derek's yang almost. Of course both of them knew what would happen if they got caught together. 

"Stiles. I'm not stupid. You're not stupid. So just ask me, what about Derek do you want to know?" Danny asked, raising his eyebrows in a questioning gesture. 

Stiles stuttered trying to come up with something to say. "What do you mean?" He started to fidget and panic. He didn't want to get Derek in trouble. He didn't know that someone other than Erica knew. "I don't know what you're talking about." Stiles crossed his arms and sat on his cot, crossing his legs. 

Danny sighed. "Stiles. Relax. You and Derek aren't exactly subtle but I'm not gonna say anything. Honestly I'm hoping you guys get together so I win the pool."

Stiles squawked. "WHAT?? There's a bet on us? Between who?"

"Erica and I but, relax. It's just a harmless joke. If I win she owes me dinner to a fancy restaurant with Ethan. Do you know how much trouble we would be in? Honestly I don't care but other people would. Stiles this is serious. But it helps that you get out in a few weeks."

"Okay." Stiles took a deep breath feeling the sense of panic leave. "I need your help. I need him to see that we should be together. I know he cares for me, but I don't think he'll even want to actually be with me? I know we could be good for each other but every time we try or get close he freaks out and I know it doesn't help that I've been in here.."

Danny gives him an apologetic stare. "I'm sure everything will work out in the end. I have to go, but I'll be back later." 

Danny went to the staff break room. The only other person that was in there was Erica. If anyone would understand the stupidity of these idiots it would be her. Danny threw himself down on the couch with a grunt and an "I can't believe these idiots". 

"Derek and Stilinski, huh?"

"What about them?"

"Don't play dumb with me Danny. I know all plus Derek has been whining for ages about him. I wish those idiots would just get over it and kiss already."

"Tell me about it, Derek seems messed up about his feelings but he knows he sure about it I guess."

"Are you thinking what I'm thinking?" asked Erica with a devilish smile. 

"God I hope so." Danny sighs

"We have got to get them over themselves and be together. Preferably after Stiles is released to avoid the trouble but at this point I don't care. But we still have to be cautious."

"We need a plan" said Erica. 

*   
Stiles was being released in a few weeks but he was still really anxious about Derek bit was hard when he wasn't there, but at the same time it was confusing when he was. 

Derek always seemed to give Stiles mixed signals about what he wanted. The kiss they shared a while ago was amazing until Derek pulled away abruptly, saying it was wrong and Stiles felt hurt, clearly being able to tell Derek kind of meant it too. 

Stiles had a lot of time to think while Derek had his days off, he learned a lot about Derek from Erica, like how used to be before he met Stiles, or funny stories from their shared shifts at work. 

Stiles wasn't confused about how he felt for Derek, and he didn't really mind that they had met when Stiles was incarcerated. He was grateful for everything Derek had done for him since they met. 

Derek was wonderful and caring and so much kinder than any of the other guards besides Erica or Danny and Stiles was really willing to give Derek as much time as he needed to let him figure out his feelings. 

*   
Stiles' time was coming to an end and he was a little disappointed, not being sure if he would see Derek again. It wouldn't be hard to find him, with all the hookups he had, but he was worried Derek wouldn't take up Stiles' offer to meet up after he was released. 

The days were winding down, surprisingly short when Derek wasn't around, but when he was they got along great. Stiles decided to try his best to stop flirting with Derek, giving him time to sort out what he feels and he has to say it's going really well. Derek seems happier, less confused and more sure of himself than he was last week. 

And somehow that made Stiles a little sad. 

*   
It was the day before Stiles was being released, and he was able to have the whole day free, (under Derek's watch of course) to spend in the courtyard of the library. Stiles chose the library, enjoying the secluded quiet and surprisingly wide collection of books to choose from. 

"Know any good books here Officer?" Stiles asked, not wanting to call Derek by his first name just incase anyone was around to hear. 

Derek glanced around, before locking the library door and covering the windows, knowing that no one really used the library anyway. The prison only kept it because it was a requirement by the state or something to give the prisoners something to do in their free time. 

Stiles closed his book as Derek took a seat beside him, their bodies facing each other. 

"Everything alright? You locked the door.." Stiles said with a confused look on his face. 

"I wanted to ask you that actually, you've been acting weird for the past few weeks did something happen?" 

Stiles shook his head and gave Derek a small smile, trying to hide the fact that he was a little hurt that Derek was happier without Stiles' constant flirting. 

Derek sighed before taking Stiles' hand in his and running his thumb over Stiles' knuckles. "Erica told me I should really think about how I felt about you and I think I understand now." 

Stiles shifted in his seat, looking down, fearing that Derek will say he doesn't feel the same. Even if he is holding his hand it's probably just for comfort that Derek is rejecting him again. 

"I couldn't see it before but now I do and Derek is okay really. I understand how you feel and it's okay.." Stiles mumbles, looking down at their hands that are clasped together. 

"You do?" 

Stiles nods. 

"Great, I wasn't sure how to say it but I want to take you out when you get out of here tomorrow." 

Stiles' lifts his head and looks Derek right in the eye. "You wanna take me on a date?"

"That's what I said yeah." 

Stiles smiles and nods.

"I'd like that."


	10. Chapter 10

**Notes for the Chapter:**

> This chapter probably sucks and for that I'm sorry but I've been packing and moving and unpacking and I'm so exhausted that I really couldn't find the effort to make this last chapter as good as I want, but if there are any mistakes they are all mine and I'm sorry.

Stiles was woke by the sound of Derek calling his name. He groaned and sat up, rubbing sleep from his eyes before looking at Derek to see he had a stack of clothes in his hands. 

"Lydia arranged for you to wear this today." Derek said, slipping the clothes through the bars of Stiles' cell. "I'll let you get changed, you'll be leaving in an hour." 

Stiles smiles to himself as Derek turns around so he can change. The suit isn't exactly what Lydia said it would be, but it looks amazing and fits great. 

He looks at himself in the shitty cell mirror, adjusting the collar of his gray button down, before buttoning up the black silk vest on top. 

He then slips on his tight black slacks that hug his ass and legs nicely before telling Derek he can turn around, before he pulls on a pair of old converse that he loves wearing while doing his dirty work. 

Derek turns and stops, eyes widening a little as he takes in the view. 

"You look great.." Derek gives a small smile before sitting down. "Really great." 

Stiles reaches through the bars and clasps Derek's hand in his own and giving a blinding smile. "I feel great Derek." 

*   
Stiles slips on his sunglasses before he exits his cell, led by Derek and followed by another guard. He can't help the smirk that appears on his face as he walks past the other prisoners, as they eat their breakfast. Their eyes are glued to his form as he walks to the other side of the building where he will get his things and leave. 

The other guard is dismissed once he gets to the door with Derek. 

"Lydia said she would be waiting outside with some of your other people.." 

Stiles pulls Derek into a hug, knowing that no one sees them. "You made my time in here better, and I can't thank you enough Derek." 

Stiles pulls away before nodding as he waits for the gates to be buzzed open. He steps outside, squinting a little bit before relaxing to the feeling of sun on his skin. He feels amazing to finally be out. 

He looks around and sees Lydia, Scott and even Allison and a few of his workers waiting for him. He turns around after taking a few steps to face Derek who is standing beside the gate. 

"I'll call you or something, if you want of course, but if you don't just you know say so and I'll go." Stiles shrugs before rubbing the back of his neck. 

He's about to step away before Derek grabs his arm, pulling him back and pressing their lips together in a frantic kiss. Stiles slides his arms around Derek's neck, pulling their bodies closer. 

Derek tries to deepen the kiss but Stiles just starts giggling causing Derek to pull away. He's confused, and has almost no idea what happened to cause Stiles' giggle fit. 

"I'm sorry did I-" 

"No no no of course you didn't it's just..I'm really happy this is happening, with you in really glad this is happening with you..I've never done this before.." 

"Really? You haven't dated before?" 

Stiles shakes his head, looking down at his shoes. "I never really had time to I guess." 

Derek smiles a little before Stiles pulled him back into a kiss. 

*A few months later* 

"Derek ugh have you seen my shoes ? I can't remember where I put them!" 

"They're by the fridge I think why would they be there anyways?"

"Because that's where I put them Derek pleaaaaaaase." 

Stiles slides his arms around Derek's waist and places a chaste kiss on the back on his neck. "You always smell so good Derek, so good." 

"I just got back from a run I probably smell awful."

"Nope. Hey Derek ?" 

"'Hmm?" 

"I'm really glad that I went to prison." 

"Prison is awful and I work there. Why?" 

"I met you and I'm pretty sure I love you..a lot" 

"I love you a lot too."


End file.
